Personne : Carreras, Virginie
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Carreras
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Virginie
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Université Laval. Département de chimie
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ncf11909919
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Publication Accès libre Asymmetric Cu1-Catalyzed Insertion Reaction of 1-Aryl-2,2,2- trifluoro-1-diazoethanes into Si–H Bonds(American Chemical Society, 2019-10-28) Ollevier, Thierry; Carreras, Virginie; Gandon, Vincent; Besnard, ClaireAn asymmetric copper(I)-catalyzed Si−H insertion reaction of 1-aryl-2,2,2-trifluoro-1-diazoethanes in dimethyl carbonate as a green solvent alternative was developed. A C2-symmetric copper(I) diimine complex enabled the asymmetric insertion reaction to give enantioenriched (1-aryl-2,2,2-trifluoroethyl)silanes with excellent stereoselectivities (up to 98:2 er). Successful conversion of the silanes into the corresponding alcohols was performed with retention of stereochemistry. Mechanistic studies and DFT calculations support the proposed model for the observed stereoselectivities.Publication Accès libre Asymmetric Diels–Alder reaction of α,β-unsaturated oxazolidin-2-one derivatives catalyzed by a chiral Fe(III)-bipyridine diol complex(ACS Publications, 2018-02-08) Ollevier, Thierry; Carreras, Virginie; Jalba, Angela; Li, MaoAn asymmetric FeIII-bipyridine diol catalyzed Diels–Alder reaction of α,β-unsaturated oxazolidin-2-ones has been developed. Among various FeII/FeIII salts, Fe(ClO4)3·6H2O was selected as the Lewis acid of choice. The use of a low catalyst loading (2 mol % of Fe(ClO4)3·6H2O and 2.4 mol % of Bolm’s ligand) afforded high yields (up to 99%) and high enantiomeric excesses (up to 98%) of endo-cycloadducts for the Diels–Alder reaction between cyclopentadiene and substituted acryloyloxazolidin-2-ones. Other noncyclic dienes led to decreased enantioselectivities. A proposed model supports the observed stereoinduction.